Trifluoroacetic acid → Ethyl 3-(2-aminoethyl)-5-[(4-fluorophenyl)methyl]benzenepropanoate

HRID 53331ノート

反応式

HRID 53331 の反応式
C(OC([NH:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:14]=[C:15]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:16]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:14]=[C:15]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:16]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 19962360Ethyl 3-[2-(t-butoxycarbonylamino)ethyl]-5-[(4-fluorophenyl)methyl]benzenepropanoate

生成物 1

HCID 19962359Ethyl 3-(2-aminoethyl)-5-[(4-fluorophenyl)methyl]benzenepropanoate収率 62.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of ethyl 3-[2-(t-butoxycarbonylamino)ethyl]-5-[(4-fluorophenyl)methyl]benzene-propanoate (2.36 g) and trifluoracetic acid (5 ml) in dichloromethane (25 ml) was allowed to stand at room temperature overnight and then evaporated. The residue was partitioned between ether and dilute sodium hydroxide solution. The organic layer was separated, washed with water and dried (MgSO4). The solvent was evaporated and the residue chromatographed on silica eluting with mixtures of dichloromethane, methanol and concentrated ammonium hydroxide. The product containing fractions were combined and the solvent evaporated to give the title compound as a gum (1.13 g), Rf 0.1 (SS 4). N.M.R. δ(CDCl3): 1.24 (3H,t), 1.48(2H,s), 2.61(2H,t), 2.73(2H,t), 2.90-2.98(4H,m), 3.93(2H,s), 4.14(2H,q), 6.88(2H,s), 6.91(1H,s), 6.96-7.03(2H,m), 7.12-7.18(2H,m).

後処理

  1. customevaporated
  2. customThe residue was partitioned between ether and dilute sodium hydroxide solution
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated
  7. customthe residue chromatographed on silica eluting with mixtures of dichloromethane, methanol and concentrated ammonium hydroxide
  8. additionThe product containing fractions
  9. customthe solvent evaporated

出典と根拠

ORDレコード
ord-e7b7a65f6f53451292f633d85295d156
出典データセット
uspto-grants-1997_04
特許番号
US05618941

反応ノート

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